An aerial view of a town with a river, buildings, and surrounding greenery.

Cat & Dog Friendly Hotels in Chestertown

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Check availability on Chestertown Pet friendly Hotels

Tonight
2 Oct - 3 Oct
Tomorrow
3 Oct - 4 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Chestertown pet-friendly hotels

A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.
Exterior
A rectangular swimming pool with a tiled edge, surrounded by lounge chairs and a concrete deck.
Exterior

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
United States
Amy
RM415
RM460 total
includes taxes & fees
1 Nov - 2 Nov
Comfort Inn & Suites Chestertown
A hotel room with a sofa, two beds, a painting, and a lamp.
A hotel room with a bed, two bedside lamps, a sofa, a small table, and a painting on the wall.
A hotel sign with a red background and white lettering, a parking lot, and a building with a brick facade.
A living room with a fireplace, a television, and a stone accent wall.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
United States
Linda
RM294
RM326 total
includes taxes & fees
8 Oct - 9 Oct
Red Roof Inn & Suites Chestertown
A row of motel rooms with stone walls and red doors.
A living room with a wooden cabinet, a television, a sofa, and a dining table.
A two-story building with a brick facade, large windows, and a sloped roof.
A hotel room with a bed, a small refrigerator, a lamp, a picture on the wall, and a curtain.

3. Driftwood Inn

Driftwood Inn
Chestertown
United States
Kathy
RM259
RM288 total
includes taxes & fees
4 Oct - 5 Oct
Driftwood Inn
Two Adirondack chairs facing a calm body of water with a clear sky above.
A reception desk with a modern design, a digital display, and a check-in counter.
A hotel room with a large bed, a desk with a flat-screen TV, a chair, a small table with a lamp, and a window with curtains.
A modern food court with a central island, various food stations, and a yogurt display.

4. Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
United States
Marc
RM421
RM467 total
includes taxes & fees
1 Nov - 2 Nov
Holiday Inn Express Annapolis East-Kent Island by IHG
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.
Marina
A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.
An outdoor event area with round tables and a view of the water.

5. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
United States
Karen
RM620
RM688 total
includes taxes & fees
13 Oct - 14 Oct
Hyatt Place Kent Narrows & Marina
A modern building with a patio area featuring outdoor seating and a fire pit.
A modern restaurant with a long counter, multiple seating areas, and pendant lighting.
A modern living room with a stone accent wall, a flat-screen TV, a dining area with a table and chairs, and a sofa with cushions.
A modern living room with a stone fireplace, wooden ceiling, and a large TV mounted above it.

6. Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
Middletown
United States
Sharon
RM486
RM540 total
includes taxes & fees
1 Nov - 2 Nov
Fairfield Inn & Suites by Marriott Middletown
A Victorian-style building with a porch, outdoor seating, and a sign for Vandiver Inn.
A formal dining room with a long table, chairs, a chandelier, and a fireplace.
A bedroom with a four-poster bed, a fireplace, a mirror, and a stained glass window.
A traditional house with a covered porch, white picket fence, and lush greenery.

7. Vandiver Inn

Vandiver Inn
Havre De Grace
United States
Mary
RM713
RM799 total
includes taxes & fees
15 Oct - 16 Oct
Vandiver Inn
A modern hotel lobby with a long dining table, several chairs, and a bar area.
A hotel reception area with a wooden reception desk, a coffee station, and framed pictures on the wall.
A hotel room with a kitchenette, a large mirror, a window with curtains, a desk, and a chair.
A hotel room with a bed, a chair, a bathtub, a framed picture, and a nightstand with a lamp.

8. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
United States
Lyn
RM348
RM390 total
includes taxes & fees
2 Nov - 3 Nov
Hampton Inn & Suites Edgewood/Aberdeen-South
A patio with outdoor seating, overlooking a marina with boats.
A marina with multiple boats docked, a Hilton Garden Inn hotel, and a parking area.
A spacious dining area with a large rectangular table, multiple chairs, and a chandelier.
A waterfront hotel with multiple balconies, a marina with yachts, and a well-lit exterior.

9. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
United States
roney
RM565
RM628 total
includes taxes & fees
19 Oct - 20 Oct
Hilton Garden Inn Kent Island Marina
A hotel entrance with a clear sign reading "LA QUINTA".
A hotel lobby with seating areas, a TV on the wall, and patterned curtains.
A modern hotel lobby with a reception desk, two computer workstations, a seating area, and a decorative vase on a table.
A hotel lobby with multiple dining tables and chairs, a reception area with a counter and a television, and large windows with red curtains.

10. La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG
Aberdeen
United States
robin
RM413
RM462 total
includes taxes & fees
12 Oct - 13 Oct
La Quinta Inn & Suites by Wyndham Aberdeen-APG
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Top Chestertown Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Excellent location. Marriott has renovated the bar downstairs; one side is a Mexican restaurant and the other is Italian. Both have great food and service."
Tammy 2-night trip
Posted 3 days ago
Annapolis Waterfront Hotel, Autograph Collection

Frequently asked questions

What's the best dog-friendly accommodation option in Chestertown?
Comfort Inn & Suites Chestertown is a top hotel for people travelling with their pets, and offers a seasonal outdoor pool and a fitness centre for its human guests. Two other good options to stay with your pet include Red Roof Inn & Suites Chestertown and Driftwood Inn.
What's the best time of year to travel to Chestertown with my pet?
When you travel with your pet, keeping tabs on the weather can make the trip safe and fun for everyone. The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.
What is there to see and do with your pet in Chestertown?
Known for its sports, Chestertown has lots to offer visitors, including its university life and festivals. See the local sights and visit Historical Society of Kent County Maryland and Chestertown Historic District. While you're there, make sure you don't miss Rolphs Wharf Marina and Northern Chesapeake Bay.

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